7-oxo-7,7a-dihydrocyclopropa[b]chromene-1a(1H)-carboxylic acid | 179067-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-oxo-7,7a-dihydrocyclopropa[b]chromene-1a(1H)-carboxylic acid
• 英文别名: 2-Oxo-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid；7-oxo-1,7a-dihydrocyclopropa[b]chromene-1a-carboxylic acid
• CAS: 179067-71-1
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: QSIZZYYLHZVVLH-UHFFFAOYSA-N

物化性质

• 沸点：
  428.2±45.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-oxo-7,7a-dihydrocyclopropa[b]chromene-1a(1H)-carboxylic acid 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 三乙胺 、 三苯基膦 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 为溶剂， 反应 15.17h， 生成 ethyl 5-(p-tolyl)benzo[b]oxepine-2-carboxylate
  参考文献：
  名称：

  通过Pd催化的碳迁移迁移和C–C键裂解形成苯并e庚因的区域专一性合成。

  摘要：

  开发了一种通过迁移插入Pd卡宾并进行C-C键裂解来合成苯并二氢萘的新方法。通过区域选择性的扩环以及在其5-位上引入芳基来构建各种苯并氧杂松。

  DOI：

  10.1021/acs.joc.5b02413
• 作为产物：
  描述：

  2-Oxo-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid methyl ester 在 盐酸 、 水 作用下， 以 二甲基亚砜 为溶剂， 生成 7-oxo-7,7a-dihydrocyclopropa[b]chromene-1a(1H)-carboxylic acid
  参考文献：
  名称：

  Chemical Switch of a Metabotropic Glutamate Receptor 2 Silent Allosteric Modulator into Dual Metabotropic Glutamate Receptor 2/3 Negative/Positive Allosteric Modulators

  摘要：

  Using an mGluR2 FRET-based binding assay, binders of the transmembrane region devoid of functional activity were identified. It is reported that slight chemical modifications of these SAMs can dramatically change activity of the resulting analogues without altering their affinities. Starting from compound 1, three mGluR2 NAMs showing also mGluR3 PAM activities were obtained. SAMs therefore represent a useful approach to explore the chemical space for GPCR allosteric modulator identification.

  DOI：

  10.1021/jm101069m

文献信息

• Regiospecific Synthesis of Benzoxepines through Pd-Catalyzed Carbene Migratory Insertion and C–C Bond Cleavage
  作者：Yang Xie、Ping Zhang、Lei Zhou

  DOI：10.1021/acs.joc.5b02413

  日期：2016.3.4

  A new method for the synthesis of benzoxepines via migratory insertion into a Pd carbene followed by C–C bond cleavage was developed. Various benzoxepines were constructed by the regioselective ring expansion concomitant with the introduction of an aryl group at their 5-position.

  开发了一种通过迁移插入Pd卡宾并进行C-C键裂解来合成苯并二氢萘的新方法。通过区域选择性的扩环以及在其5-位上引入芳基来构建各种苯并氧杂松。
• Chemical Switch of a Metabotropic Glutamate Receptor 2 Silent Allosteric Modulator into Dual Metabotropic Glutamate Receptor 2/3 Negative/Positive Allosteric Modulators
  作者：Stephan Schann、Stanislas Mayer、Christel Franchet、Mélanie Frauli、Edith Steinberg、Mireille Thomas、Luc Baron、Pascal Neuville

  DOI：10.1021/jm101069m

  日期：2010.12.23

  Using an mGluR2 FRET-based binding assay, binders of the transmembrane region devoid of functional activity were identified. It is reported that slight chemical modifications of these SAMs can dramatically change activity of the resulting analogues without altering their affinities. Starting from compound 1, three mGluR2 NAMs showing also mGluR3 PAM activities were obtained. SAMs therefore represent a useful approach to explore the chemical space for GPCR allosteric modulator identification.